A universal struggle for social sector leaders is creating a vision, and then moving everyone toward that vision within a resource-constrained environment. Many people believe funding is the primary constraint. But another factor puts an equal if not stronger pressure on organizations: time.

Usually, a specific staff member is responsible for fundraising and financial management. Time management, however, doesn’t live within one job description and rarely receives the attention it needs. This is notable because in mission-oriented organizations, urgency is a driving factor. Yet research indicates that organizations complete fewer than a third of projects on time.

Whether you are a social entrepreneur leading a startup or a manager in a national nonprofit, the tension between the statistical truth and your mission can lead to consistent frustration. Further complicating the situation is the reality that those same odds apply to you as a leader.

Leaders who catch up

For the past 10 years, I’ve advised social sector leaders across the country on a range of topics. No one ever says, “My team is behind, but I’m ahead.” It’s quite the opposite. Most leaders acknowledge that they are behind on their own work as well.

This is not for want of trying. Strong social sector leaders borrow across industries and leverage management practices commonplace in other sectors, including:

  • Project management. They focus on creating well-defined objectives, prioritization, and clear reporting structures.
  • Feedback. They ensure that communication channels exist in all directions and build feedback into the process.
  • Delegation. They discuss work streams and potential re-distribution to create balance across the team.

But that isn’t enough. Whether it’s donor pressure, local politics, lack of infrastructure, or daily firefighting, issues compound. Eventually, leader and team alike fall behind.

For many, that dynamic increases their stress. Others view the ticking clock in a different way. This group has come to terms with what psychologists Daniel Kahneman and Amos Tversky call the planning fallacy. Kahneman’s research shows that people, by nature, aren’t good at assessing their own ability to manage time.

The way leaders view this phenomenon determines their success. The best leaders believe not completing projects on time is unacceptable. But they expect to fall behind during a project. To them, being on track is only half the puzzle. The other half is knowing how to catch up. These leaders:

1. Look for and encourage pessimism

In the social sector, leadership that empathizes and uplifts is the ideal. It is interesting, then, that leaders who know how to catch up understand the power of pessimism.

To be clear, they are not pessimistic leaders. Rather, they want anyone who is behind to display pessimism. Optimism is the enemy when you are behind and often the reason for missed deadlines in the first place.

When these leaders detect pessimism, they know it is a good sign. Studies show people are more likely to make accurate assessments and take action when they are pessimistic about reaching their goal. If they detect optimism, these leaders steadily express doubt about the options team members put forth to push them in a more realistic direction.

These moments are not the touchy-feel version of servant leadership. They are about pragmatism. As you develop plans for catching up, use pessimism to cut through disillusions and create clarity about next steps. Once you enter execution mode, then shift back to inspiration and encouragement.

2. Discuss problems, not solutions

Most leaders prefer their team to come with solutions, not problems. In terms of catching up, these leaders want the opposite. Research has shown that discussing problems is more effective at reducing miscalculations than focusing on solutions.

These leaders not only discuss obstacles, they push for specifics. A manager on deadline for a community engagement project once described an example of this to me. One of her team member had said, “Just trying to catch the local pastor will cost us two days.”

She pushed for details, “What exactly happens during those days?”

The team member explained, “I’ll email, no response. I’ll call, leave messages, no reply. I usually end up reaching his father who is always at the church. He’s the one that gets the pastor to call back.”

The team decided to call the pastor’s father as the first step instead of the last.

This seemingly obvious solution became clear only because detail forced an accurate portrayal of events. When catching up, dive into problems and ask for specifics. It allows teams to cut the fat. It creates agility and quickens the pace of the work to come.

3. Make time salient

Depending on your vantage point, time moves differently. Looking backward, time is fixed. In the future, it is infinite and never in shortage. Time is a slippery thing, and leaders who catch up are adept at making it easier to grasp.

Research indicates that people put in longer hours as they get closer to deadlines, but they begin that adjustment too late. One team I worked with shared that the days preceding their due dates were “all-nighters,” and it wasn’t uncommon to ask the funder for extensions. At one point, the manager was forced to take over grant reporting mid-stream. The manager shared the team’s process map with friends who lead similar work. The response was always a knowing chuckle followed by, “Add three days here and here.”

Based on these longer predictions, the organization’s imminent deadline became impossible. “All-nighters” seemed inevitable. Then he realized longer days don’t need to be bunched up near the deadline. He blocked a few more work hours weekly during the remainder of process. As the deadline neared, the team was ahead and had less stress, and extension requests are now a thing of the past.

Whether mid-stream or at the start of project, use the longest time historically taken to predict the future time needed. If the result overshoots your deadline, redistribute and front load work immediately. This will provide some buffer, and you’ll be less subject to last-minute scrambles.

Like all strong leaders, those who know how to catch up take measures to keep work on schedule from the start. They also know planning is based on incomplete information not revealed until the project begins. They understand that it’s highly likely that they will fall behind. They view human behavior as a set of probabilities.

What separates them is a mindset geared to playing those odds. As a result, their strategies for managing the intersection of work and time seem counterintuitive. But adopt their approaches, and the next time you fall behind, you’ll be better equipped to come out ahead.

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